Diazepines. IV. Synthesis and Biological Action of 6-Phenyl-4H-imidazo [1, 2-α] [1, 5] benzodiazepin-5 (6H)-ones

摘要: A series of 6-phenyl-4H-imidazo [1, 2-α] 5] benzodiazepin-5 (6H)-ones (1) was synthesized starting from 2-nitrodiphenylamines (9) and evaluated for CNS activity. Bromoacetylation 9 to N-bromoacetyl-2-nitrodiphenylamines (10) subsequent treatment 10 with sodium cyanide gave N-cyanoacetyl-2-nitrodiphenylamines (11) which were also prepared directly by cyanoacetylation. The reduction the nitro group 11 give 2-amino-N-cyanoacetyldiphenylamines (12) followed cyclization 12 HCl afforded 4-amino-1-phenyl-2H-1, 3-dihydro-1, 5-benzodiazepin-2-ones (13). Treatment 13 propargylamine in presence p-toluenesulfonic acid or α-bromoketone 1. Some 1 α-aminoaldehyde acetal amidine derivatives 14 their formic acid. Although ED50 antipentetrazole activity 8-chloro-2-ethyl-6-phenyl-4H-imidazo (6H)-one (1h) 5.5 mg/kg, ratio muscle relaxant that taming 1h fairly large compared those diazepam.